Saving Private Whitman
by ElizabethDarcy78
Summary: Lieutenant Donald Francis Draper resolves to help Private Dick Whitman have a better life. AU. Dick Whitman, Lt. Donald F. Draper, Anna Draper, Adam Whitman, Betty Hofstadt, Roger Sterling, Pete Campbell, Freddy Rumsen, Joan Holloway, Peggy Olson. Rated M for sexual content. *STORY NOW COMPLETE, **I OWN NOTHING. MATTHEW WEINER AND LIONSGATE OWN EVERYTHING.
1. Chapter 1

**Saving Private Whitman**

(AKA, Dick Whitman pays it forward)

* * *

Blurb: Lieutenant Donald F. Draper resolves to help young Dick Whitman have a better life. AU. Dick Whitman, Lt. Donald F. Draper, Anna Draper, Adam Whitman, Betty Hofstadt, Roger Sterling, Pete Campbell, Freddy Rumsen, Joan Holloway, Peggy Olson. *I OWN NOTHING. MATTHEW WEINER AND LIONSGATE OWN EVERYTHING.

* * *

**Author's Notes: Dick Whitman (in my mind anyway) is a MUCH better guy than the Don Draper we all know and love/hate. Bear this in mind as you read this story.**

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**Chapter 1**

**Korea, 1950**

Lieutenant Donald Francis Draper had nearly finished his tour of duty in the army when he was assigned to set up a field hospital in Korea. He was relieved that he wasn't being sent to the front lines to fight during the three months he had left before he was to be discharged. He knew that it would require a lot of manpower to build the hospital and dig the trenches so he asked for twenty soldiers to be sent to help him with the assignment. When the transport vehicle arrived carrying only one soldier, a twenty four year-old Private by the name of Dick Whitman, Lt. Draper couldn't have been more disappointed. "This is going to take a month when it should only take a few days!" He exclaimed.

Digging the trenches was a slow and arduous task, but Pvt. Whitman was a good worker and was always very respectful. Lt. Draper could tell that Whitman had some experience working with his hands and he was pleased to see that the kid never complained. Whitman hardly ever spoke and when he did it was like pulling teeth to get him to talk about himself. The little information Lt. Draper was able to glean from him was that Whitman had lived on a farm as a boy, but he was not forthcoming about what he had been up to prior to volunteering for service.

One night before they were going to turn in for the evening, Lt. Draper asked Pvt. Whitman what had compelled him to volunteer for service.

"I had to get out of there sir." Dick said.

Lt. Draper was confused and asked, "What could have been so bad that you would rather risk you life half-way around the world than be safe at home with your family?"

Dick took a deep breath and swallowed before speaking. "I am an orphan sir, I have no real family."

Don frowned, "I'm sorry to hear that. If you don't mind me asking, what happened to your parents?"

"My mother died having me, and my father was kicked by a horse when I was ten years old." Dick said quietly.

"Jesus, Whitman that's terrible!" Don exclaimed. "I'm sorry, I don't mean to pry, but who have you been living with since then?"

Dick shook his head. "It's fine sir. My stepmother was with child and we went to live with her sister in Pennsylvania."

"Was it a nice place?" Don asked.

Dick shook his head. "Not really. it was a house of...ill repute."

Don's eyes widened in surprise. "You were raised in a whorehouse Whitman?" Don said incredulously.

Dick looked down in shame. "Yes...Lieutenant, if you don't mind I'd like to get some sleep."

Lt. Draper could tell that he had hit a nerve and he didn't want to press the kid any further right then. "Certainly Private. Get some rest kid, I'll keep watch."

Lt. Draper was able to find out a few more facts about Dick while they worked digging the trenches. Dick reluctantly shared that his mother had been a prostitute herself, and that when she died, Dick had been given to his father and stepmother to raise. He also shared that his stepmother resented him and never let him forget that he was a 'whore child'. Dick also admitted that his father and stepmother both beat the hell out of him. Don felt terrible for the kid and he could only imagine how miserable Dick's childhood had been.

Despite Dick's troubled past, he was a good kid and he had a good head on his shoulders. After a month or so, they had completed digging the trenches and began assembling the structures that were to become the field hospital. Lt. Draper was grateful that the army had sent Dick to him, because their assignment may not have been as successful if the army had sent a different soldier.

**Two Months Later:**

It was with great relief that Lt. Draper finished his tour and was being sent back to the United States. He was looking forward to returning home to his wife and his real career designing swimming pools...a far cry from digging trenches in the battlefield. It was with regret that he left Pvt. Whitman, who would likely end up seeing real action soon. The closest they had come to combat during the last three months was when the enemy had fired on them in broad daylight and then disappeared. They hid from the enemy in the newly dug trenches, but poor Whitman had pissed himself. Lt. Draper hoped that if his young friend did go into battle, that he would fare well.

Lt. Draper had grown quite fond of the gangly kid. He felt sorry for him. It seemed like Whitman had been dealt a poor hand and never had a fair shot. The thought that a life in the army was a step up for him was mind boggling. Lt. Draper had no idea how long this conflict would continue, but he hoped that when it ended and if Pvt. Whitman survived, that he might be in the position to help the young man have a shot at a better life.

As they rode in the transport vehicle that was taking Dick to his new assignment and Lt. Draper to the base where he would eventually head home, Lt. Draper had a few things he wished to say to the young soldier.

"Listen kid, there is no reason that you have to go back there...to that place where you grew up. I know you feel like you owe them, but you don't. Send them money if you want, help out your brother when he's old enough but please don't go back to that place. When this is all over and you get discharged, please look me and the Mrs up. We're in San Pedro, California. You can stay with us and come work for me. I always need men like you who are willing to work."

Lt. Draper handed Dick a piece of paper with his name and address on it. "I'm serious, Dick. Look me up."

Dick looked the older man in the eyes and smiled, grateful that his superior had taken an interest in him. "Thank you sir, I will." Dick said gratefully.

Lt. Draper slapped Dick on the back in encouragement. "You're going to be fine kid. Just keep your head down and don't do anything stupid."

Dick grinned, "I'll try not to sir."


	2. Chapter 2

**Saving Private Whitman**

(AKA, Dick Whitman pays it forward)

* * *

Blurb: Lieutenant Donald F. Draper resolves to help young Dick Whitman have a better life. AU. Dick Whitman, Lt. Donald F. Draper, Anna Draper, Adam Whitman, Betty Hofstadt, Roger Sterling, Pete Campbell, Freddy Rumsen, Joan Holloway, Peggy Olson. *I OWN NOTHING. MATTHEW WEINER AND LIONSGATE OWN EVERYTHING.

* * *

**Chapter 2**

**California, 1952**

Corporal Dick Whitman had never been more grateful to step off a plane than he was when he landed in California. He smiled broadly when he spied his former commanding officer standing with a blonde woman among the crowd of well wishers.

"So, you made it back in one piece! Not always an easy feat. Welcome home Corporal!" Don said happily as he hugged his old friend.

"Thank you Lt. Draper! Thank you for taking me in! You don't know what this means to me!" Dick said sincerely.

Don shrugged off Dick's effusive gratitude. "There will be no more of that. And I'm a civilian now, so please call me Don. Come on, I want you to meet my wife. Anna, this is Corporal Richard Whitman, the young man I've been telling you about all these years."

Anna smiled warmly. "Pleased to meet you Corporal. I've heard so much about you."

Dick smiled and shook the woman's hand. "The pleasure is all mine Ma'am. And please, call me Dick."

Dick had filled-out quite a bit since the last time Don had seen him, and he had grown into a very handsome man. Dick cut an impressive figure in his dress uniform and Don noticed with amusement that several of the young ladies in the crowd were staring unabashedly at him. Gone was the scrawny kid he first met two years earlier, and in his place was a well built man who had seen more of the evils of the world than anyone should have at such a young age.

Dick had exchanged letters with his former commanding officer during his time in Korea but he was unaware that the Drapers' modest house was near the beach. Dick was overjoyed because apart from flying over it, he had never really seen the ocean. Dick took a few days off for rest and relaxation and he went to the beach and swam in the ocean. He didn't feel comfortable doing nothing while his hosts went about their usual routines...Anna was a piano teacher and Don was a structural engineer, so he was ready to begin working for Don fairly quickly.

Dick worked tirelessly from nine to five and returned home and enjoyed the company of Anna and Don. Dick especially enjoyed getting to know Don's wife Anna. Dick opened up quite a bit to her, revealing more about himself to her than he ever had to anyone before. Dick admitted to Anna that he had never felt loved by his father or step-mother. He also told her that he had every intention of helping his half-brother Adam get away from home as soon as it was possible. Anna in turn confessed her insecurities to Dick...how she felt that she had let Don down by not being able to bare him any children and carry on the Draper name. Dick assured her that wasn't true and told her about how fondly her husband had spoken of her when they were overseas.

Dick had a tremendous amount of respect for Don and his wife and he aspired to have a life similar to theirs some day. The Drapers had a wonderful marriage. Don and Anna had a true partnership, and that was the kind of marriage that Dick wanted. He also desired to one day have a family and eventually own his own home. All of these ideas had previously felt unrealistic, but because of the generosity of the Drapers, they now felt within his grasp.

One day after living with the Drapers for a few months, Don asked Dick if he had ever thought about what he would like to do for a career.

"I don't know sir...why do you ask?" Dick asked.

"Well, I've been watching you Whitman, and you're not like the other men who work for me."

Dick was alarmed. "Oh, how so?"

Don chuckled. "Relax Dick, it's nothing to worry about. You're a smart kid and you've got a good head on your shoulders. I think with a little more education you could really make something of yourself. How much schooling do you have if you don't mind me asking?"

Dick was ashamed. "I didn't finish high school."

Don nodded in understanding. "I have a suggestion for you. You should go to night school and get your high school equivalency, and then you can get a better idea of what you are good at and what you would like to pursue as a career. You don't want to spend the rest of your life digging holes do you?"

Dick chuckled, "No, I guess not. But how would I pay for it? Where would I live?"

"You can continue to live here and work for me for as long as you want. Anna loves having you here. For so long it's been just the two of us and she was so lonely when I was oversees. I know she thinks of you as the little brother she never had. Anyway, just think about it. I know that you can do something special, kid."

Dick was touched by Don's generosity. He couldn't believe that the Drapers thought so much of him. He had never experienced such unconditional love and support before.

Dick took Don's advice and enrolled in night school classes. He completed the necessary coursework for his high school equivalency and in the process discovered that he had a real talent for writing. Dick continued to work for a Don during the day and he began taking writing classes at the local community college at night. He also took the opportunity to take some art classes, some additional math and business classes and he also learned to type. Dick knew that he would be eternally grateful to the Drapers for giving him the opportunity to get an education and have a better life. He didn't want to think about what he would be doing if if he had returned home to the brothel in Pennsylvania.

After about a year and a half, Dick knew that it was time for him to move out and try to make it on his own. He thanked the Drapers for their hospitality and promised to stay in touch. The Drapers were the first real positive adult influences that he had ever had. They were two of the most selfless people he had ever met and he knew that he would spend the rest of his life trying to find a way to repay them for their generosity.


	3. Chapter 3

**Saving Private Whitman**

(AKA, Dick Whitman pays it forward)

* * *

Blurb: Lieutenant Donald F. Draper resolves to help young Dick Whitman have a better life. AU. Dick Whitman, Lt. Donald F. Draper, Anna Draper, Adam Whitman, Betty Hofstadt, Roger Sterling, Pete Campbell, Freddy Rumsen, Joan Holloway, Peggy Olson. *I OWN NOTHING. MATTHEW WEINER AND LIONSGATE OWN EVERYTHING.

* * *

**Author's Notes: There is some dialogue in this chapter that comes directly from the Episode "Waldorf Stories". **

* * *

** Chapter 3**

Dick bid adieu to the Drapers and hopped onto a bus bound for New York City. He felt that New York was as good as any place to begin a new life. He also wanted to move closer to his brother Adam. Dick hoped that when Adam turned eighteen, that he could provide a place for his brother to live so that he could get away from that bordello. Dick hoped to be the kind of positive influence on his brother that the Drapers had been for him.

Dick found a very small and inexpensive apartment in the city and he found a job selling used cars. Dick was a natural salesman and he discovered that he was very good at the art of persuasion. Dick had one of the best sales records at the dealership and he was able to earn a decent living. He was very excited when he was also was given the opportunity to write local ad circulars for the dealership.

After a while, Dick grew restless selling cars and decided to move on, and he found a job selling furs at a fur company. The job also offered him the opportunity to write ad copy for the store. Dick displayed a real talent for this and his boss was overjoyed to have such an asset working for him.

In early 1954, Dick met a young model by the name of Elizabeth "Betty" Hofstadt while on a photo shoot for the fur company. Dick was smitten and asked her out to dinner. Betty initially declined, but after Dick spent a significant amount of his paycheck on the fur coat that she was taken with, she agreed to go out with him. Dick thought Betty was the most beautiful woman he had ever seen. She smiled all the time and she was the spitting image of a young Grace Kelly. Betty thought Dick was very handsome and quite charming.

On their first date, Dick learned that Betty came from a wealthy Philadelphia family. Betty's father had fought in The Great War and Betty was the oldest of two children. Betty explained that she had recently graduated from Bryn Mawr with a degree in Anthropology, and that she had been modeling for a few months. Betty's mother did not approve of her first born child modeling, but Betty had defied her mother's wishes and had enjoyed seeing a bit of the world.

Dick told Betty a little about himself, explaining that he was raised on a farm in Illinois during the Depression, and that after his father died and they lost their farm that his family moved to Pennsylvania. He left a few details out, figuring that Betty didn't need to hear all of the sordid details of his childhood on their first date. Dick explained that he had served for two years in Korea and that his goal was to get a job working at a Madison Avenue advertising firm.

Dick and Betty went out several times and Dick fancied himself in love with her. Betty was very fond of Dick, but knew that her parents would not approve of him. It turned out she was right and Betty's father threatened to cut off all financial support to her if she didn't stop seeing Dick.

"I will not have my only daughter saddled to some yokel! He has no people! You can't trust a man who has no people!" Betty's father exclaimed.

"Daddy," Betty pleaded, "Dick is a good man. Who cares if he comes from nothing. He's a self-made man."

"I won't stand for it Elizabeth! You would be selling yourself short. If you insist in being with him, then you will have to go it alone without any help from your mother and I."

Betty broke things off with Dick shortly thereafter. Dick was heartbroken, but he remembered something that his friend Anna Draper told him. She had said that the right girl wouldn't care about Dick's background and would be able to see what a good and loyal person he is. She also advised him never to rush into anything. He should take his time to really get to know the girl before making any sort of commitment. She also said that he would know when he'd met the right one because he would feel it. There wouldn't be any hurdles, it would just be easy.

Dick's pride was wounded, but he didn't let this setback break his spirit. He continued working at the fur shop and one day opportunity knocked in a way he never expected. An executive came in shopping for a fur coat for his "special lady". The gentleman noticed one of the posters featuring Betty Hofstadt hanging up in the store and commented on it.

"'Why wait for a man to buy you a fur coat?' That's a dumb question. Who does your work?"

"I do." Dick replied.

"Really?" The gentleman asked.

"Yeah. It's an interest of mine, and they let me do it."

The gentleman gave Dick his card. Dick was surprised to see that the gentleman was the president of Sterling Cooper, a successful advertising agency.

Dick smiled, "Look at that! Can I give you a call?"

The gentleman frowned, "First of all, you need twenty of those. And second of all, no. I just want you to call that number so I can give you some very specific delivery instructions."

Dick nodded, "Of course Mr. Sterling."

As the gentleman was leaving the store, Dick asked him politely if he would be willing to look at his book, as he was an aspiring copywriter. The gentleman, being in a good mood told Dick to call his secretary to set up a meeting for the following week.

Dick eagerly prepared his portfolio, filling it with his finished work as well as ideas he had for other products. The executive whose name was Roger Sterling was impressed with the younger man's work and his tenacity and offered him a job as a junior copywriter. Dick quickly distinguished himself as a very talented copywriter and he moved up the ranks with relative ease. He established a firm friendship with fellow writer Freddy Rumsen and he eventually drew the notice of the agency's other senior partner, Bert Cooper, who promoted him to the position of Senior Copywriter.

Dick often felt out of place among the other executives at Sterling Cooper. The vast majority of the executives hailed from ivy league backgrounds and Dick knew that he could never pretend to have that sort of pedigree. Dick just continued to work hard and tried not to allow his feelings of inferiority get the better of him. Dick's diligence and hard work paid off. Within six years he had been promoted from a lowly Junior Copywriter to Creative Director.

Dick had dated a series of women off and on during that time, but there had been no one serious since Betty. The closest he had come to having a serious girlfriend had been a beautiful free-spirited brunette named Midge Daniels, an artist who lived in the Village. They had loved each other, but she had not been willing to settle down and make a commitment and Dick still desired to one day have a wife and family. Now in his mid-thirties, Dick knew he wasn't getting any younger and he was actively searching for the woman who would be willing to become Mrs. Dick Whitman. Numerous secretaries had thrown themselves at him, being one of the more attractive and eligible bachelors in the office. But Dick had a strict rule for himself about not having any dalliances with anyone from work. This led to many tears and as a result Dick had gone through a number of secretaries over the years.

As he moved up the ladder at Sterling Cooper, Dick moved into a larger apartment. He had sent a portion of his paycheck home to his family ever since he returned from Korea in order to help them out as much as possible. In 1958, he received word that his brother Adam's mother had passed away. Dick sent for Adam and invited him to come and live with him in New York. Dick wanted to extend the same courtesy to his brother that the Drapers had done for him. At the age of twenty-two, Adam was able to find a job working as a janitor and he went to school at night to get his high school equivalency, just like his older brother had. Dick was happy to have family around and he was pleased to be able to help his brother have a shot at a better life.


	4. Chapter 4

**Saving Private Whitman**

(AKA, Dick Whitman pays it forward)

* * *

Blurb: Lieutenant Donald F. Draper resolves to help young Dick Whitman have a better life. AU. Dick Whitman, Lt. Donald F. Draper, Anna Draper, Adam Whitman, Betty Hofstadt, Roger Sterling, Pete Campbell, Freddy Rumsen, Joan Holloway, Peggy Olson. *I OWN NOTHING. MATTHEW WEINER AND LIONSGATE OWN EVERYTHING.

* * *

**Author's Note: This contains dialogue for the episode "Smoke Gets In Your Eyes".**

* * *

**Chapter 4**

In February of 1960, shortly after having been promoted to his new position Dick was assigned a new secretary named Peggy Olson who was twenty-one years old and fresh out of secretarial school. Peggy was a pretty little thing with beautiful blue eyes. Unlike the other secretaries who clearly dressed to attract the male executives, Peggy dressed very primly, almost like a schoolmarm. Dick sensed right away that Peggy was a kindred spirit of sorts. Like him, Peggy was very serious about her job, and she was very committed to always doing her best work. She was different from the other secretaries he'd had in the past in that and she wasn't a giggly, simple-minded girl. It was apparent to him right away that she probably didn't have a lot of money which he could definitely relate to. Dick thought there was something sweet and innocent about Peggy that he was drawn to...perhaps it was the earnest look in her blue eyes. Whatever it was, for the first time since he had been working at Sterling Cooper he had to remind himself of his rule that his secretary was off limits.

The junior executives took notice of the new girl as they always did. They made eyes at her as they walked by her desk and made comments to her full of innuendo. But only one of them seemed to be making it his goal to get the new girl into bed as soon as possible, and that was Pete Campbell.

Pete Campbell was a twenty-six year-old junior account executive who hailed from Dartmouth. He had worked at Sterling Cooper for three years and he was the unofficial ring leader of the young junior executives which included Ken Cosgrove, Paul Kinsey and Harry Crane.

Dick did not like Pete Campbell. Pete was from a wealthy family and he felt he was entitled to have whatever he wanted with little effort. Dick resented this attitude since he had worked hard for everything he had achieved, having truly started with nothing. Dick knew that Pete was jealous of his recent promotion, apparently feeling that he was qualified to be Creative Director despite never working a day in Creative. Pete always seemed to be competing with him for one thing or another. Dick for the most part ignored Pete and his superior attitude, but when he noticed Pete sniffing around Peggy, Dick felt protective and territorial. He was worried that Pete would try to bed his secretary simply to one-up him, since it was well known that Dick wouldn't touch any of the secretaries. Dick had no intention of starting anything with Peggy, but he felt as though he needed to protect the young girl's virtue.

On Peggy's first day, Pete lurked around Dick's office and proceeded to flirt awkwardly with her.

"So Whitman, who's your little friend here?" Pete asked looking up and down Peggy's body in a predatory manner.

Dick's hackles immediately went up. "My 'little friend' as you called her is my new secretary. Pete Campbell, I'd like you to meet Peggy Olson."

"How come you always get the new girl?" Pete asked.

"Management gets all the perks." Dick said drily.

"Where are you from honey?" Pete asked Peggy.

"Miss Deaver's Secretarial School." Peggy replied.

"Top notch. But I meant where are you from? Are you Amish or something?"

"No. I'm from Brooklyn."

"Well, you're in the city now. It wouldn't be a sin for us to see your legs. If you pull your waist in, you might look like a woman."

Dick could tell immediately that Pete had offended the girl. Peggy's face turned bright red and she cast her eyes downward.

"Will that be all Mr. Whitman?" Peggy asked with a wary glance at Pete.

Dick nodded. "Yes, Peggy. I'd like to apologize for my colleague here. It appears that he left his manners back at the fraternity house." Peggy smiled demurely at Dick and left the office and closed the door behind her.

Once Peggy had left, Pete began again. "So Whitman, do I get first crack at her? Word is she took down more sailors than The Arizona."

"Has Roger Sterling heard you talk like that? You should watch how you talk to people." Dick said angrily.

"Christ, Whitman, are you already sleeping with her?" Pete said incredulously. "She's a little young for you, and I thought you were supposed to be too virtuous for all of that. This girl must be something special."

"Aren't you getting married this weekend Campbell?" Dick asked Pete pointedly.

Pete twisted his face into a sneer. "Yes I am, but just because I'm off the market that doesn't mean that I can't browse what is on display now and then. By the looks of it, that girl would be ready for a good go-around anytime."

Dick frowned and shook his head in disgust. "Here's a word of free advice Mr. Campbell. Advertising is a very small world, and when you do something like malign the reputation of a girl from the steno pool on her first day, you make it even smaller. Keep it up, and even if you do get my job, you'll never run this place. You'll die in that corner office, a mid-level executive with a little bit of hair who women go home with out of pity. You want to know why? because no one will like you."

"Who do you think you're talking to!" Pete said angrily. "I know all about you, Whitman. I know that you are a nobody from out in the sticks who practically fell off of the turnip truck."

Dick shrugged, "That may be true Pete, but all of the breeding and money in the world cannot make up for what a deep lack of character you have."

Pete made an excuse and stormed out of Dick's office. He passed Peggy's desk without a word and retreated to his own office for a drink.

Peggy returned to Dick's office after Pete left and they exchanged wary glances. Dick grimaced, "I would like to apologize once again for my colleague's behavior. Hopefully I don't have to tell you to stay away from Mr. Campbell, Peggy. Whatever limited charms he may posses on the surface are negated by his personality. I know it's probably flattering to receive attention from a good looking young junior executive, but I can assure you that you do not want to be involved with him. He is not a good man. You can do much better Peggy."

Peggy blushed at her employer's kind words. "Thank you Mr. Whitman" Peggy said appreciatively. "This has been a very confusing day to say the least."

"Oh?" Dick said, intrigued. "I think you've done very well for your first day! Did something else happen? You can tell me. I am your boss but that doesn't mean we can't be friendly."

Peggy took a deep breath. "Well," she began, "Miss Holloway implied that my only goal as a secretary should be to marry an executive and move to the suburbs. It's not that I don't want to get married someday, but that's not why I'm working here. She also criticized the way I dress, suggesting that I need to show myself to more of an advantage. I don't have a lot of money to spend on clothes, and frankly that isn't my priority right now. I just want to keep my head above water and do the best I can. I'm not Joan and I don't want to be."

Dick smiled. He admired Peggy's spunk. "Peggy, why don't you let me buy you lunch. Come on, it's your first day." Peggy smiled. "Okay Mr. Whitman."

Dick took Peggy to a nearby diner where they had a very pleasant lunch. Dick asked Peggy to tell him a little bit about herself. Peggy explained that she was from Brooklyn, that she was raised Catholic and that she was the youngest of two siblings.

"My mother doesn't like me working in the city. She's worried that I'm going to fall in with the wrong sort of people." Peggy revealed.

"What about your father?" Dick asked.

"He passed away...right in front of me actually. I was the only one home. He was listening to some football game on the radio. That's why I don't like sports."

Dick furrowed his brow, "I'm sorry to hear that. My father died right in front of me too...kicked by a horse."

Peggy snorted uncomfortably. "Seriously?" Dick nodded. "What about your mother?" Peggy asked.

"I never knew her. She died when I was born." Dick said sadly.

Dick revealed that his half-brother Adam was living with him in the city while he worked and went to school.

"He's a few years older than you I think. He's a good kid, he just needed a fresh start and to get away from home. There were no opportunities for him there. At least he didn't have to join the army like I did to get out."

"Where is home?" Peggy asked innocently.

"Pennsylvania, by way of Illinois. We lost our farm and had to move in with my stepmother's sister in Pennsylvania."

"I'm sorry to hear that. It's nice that you're looking out for your brother. He's lucky to have you."

Dick smiled. "Thank you. I'm happy to do it. He's the only family I have left."

Dick enjoyed getting to know Peggy. She was very smart and easy to talk to. He felt very comfortable around her.

They returned to the office and finished the rest of the day's work. Peggy came over to Dick at the end of the day and placed her hand innocently over his on the desk.

"Thank you for a wonderful first day Mr. Whitman." Peggy said sweetly. Dick flipped his hand over and squeezed her hand. "It was my pleasure." There eyes met and Peggy's stomach fluttered. "I'm looking forward to working with you Peggy." Dick said sincerely.

Peggy knew that she needed to be careful because it would be fairly easy to fall for her handsome boss. She knew that the situation was hopeless and that she should forget about the possibility of him returning her feelings. She had been told numerous times on her first day that Mr. Whitman never dated anyone from the office. Miss Holloway had told her that Mr. Whitman was a mystery to everyone because he had never hit on any of the secretaries, specifically the undisputed bombshell of the office, herself. The rumor around the office was that Mr. Whitman simply wasn't interested in women. Peggy wasn't sure that was true. She thought that he might be a very moral man who wished to keep his work and private lives separate. She could certainly understand why many of the women in the office mooned over her boss. He was very handsome and he appeared to be a very kind man. Peggy did think it was a little odd that he was still unmarried, but neither was their art director Mr. Romano and he was older than Mr. Whitman. Perhaps he just hadn't met the right woman. He had alluded to having a difficult childhood so perhaps dating hadn't ever been a priority for him.

A few days later, Peggy was able to observe her boss in the presence of one of their new clients..a beautiful woman named Rachel Menken. Peggy thought that he was enamored with Miss Menken and she wasn't surprised later when Dick asked her to schedule a dinner date with her. Peggy felt a little jealous, but she knew she was being ridiculous. Dick was her boss and she was just his mousy little secretary.. Plus Miss Menken was a glamorous, wealthy woman and was a real catch. Peggy knew she couldn't compare, but she had just secretly hoped that if Dick had decided to start dating that he would have picked her.


	5. Chapter 5

**Saving Private Whitman**

(AKA, Dick Whitman pays it forward)

* * *

Blurb: Lieutenant Donald F. Draper resolves to help young Dick Whitman have a better life. AU. Dick Whitman, Lt. Donald F. Draper, Anna Draper, Adam Whitman, Betty Hofstadt, Roger Sterling, Pete Campbell, Freddy Rumsen, Joan Holloway, Peggy Olson. *I OWN NOTHING. MATTHEW WEINER AND LIONSGATE OWN EVERYTHING.

* * *

**Chapter 5**

**One Month Later**

Dick was couldn't have been more pleased with his new secretary Peggy. She was an extremely competent secretary and a very diligent worker. She could usually anticipate his needs before he even thought of them. He also appreciated that he could actually speak with her about things other than work. They had eaten lunch from the cart together several times during Peggy's first month of work and he had enjoyed getting to know her better.

Peggy told him several amusing anecdotes about her childhood, usually involving the antics of her and her sister Anita. Dick shared some of the few pleasant memories that he had from growing up on the farm in Illinois. He told her a few of the sadder stories as well. In a short amount of time, their working relationship had developed into a close friendship. Dick felt closer to Peggy than he did to anyone else in that office. He had to keep reminding himself that to form any sort of romantic attachment to her would be inappropriate, but it was getting more difficult by the day to maintain his resolve.

In an attempt to take his mind off of his secretary, Dick continued to date women outside the office. Unfortunately he had been unable to form any sort of real connection with a woman that compared to what he had with Peggy. He had taken Rachel Menken, the daughter of the owner of Menken's Department Store out to dinner in an attempt to convince her to sign with Sterling Cooper. Although she was extraordinarily beautiful and very intelligent, he simply wasn't interested in her romantically.

The other women he dated all seemed fairly superficial when he compared them to Peggy. Regardless of his feelings, Dick was determined to keep things with her professional, if only because he didn't want to lose the best secretary he had ever had. Dick found that he was relieved when he saw one of the younger copywriters approach her and ask her out. While he felt a little jealous of the attention the younger man received, he knew that it was for the best.

As the "new girl" Peggy had received a fair amount of attention from the young junior executives. She was grateful that Pete Campbell hadn't bothered her since her first day of work. Ken Cosgrove took her to lunch once and she enjoyed his company but she was by no means smitten with him. She did go out with Paul Kinsey, one of the junior copywriters a few times, and while it wasn't a love match she did have a nice time with him. He took her to dinner and they went dancing. Unfortunately, Paul seemed almost more interested in learning about her mysterious boss than about herself. Peggy didn't divulge any information to Paul about Dick, knowing how much her boss valued his privacy and the loyalty of those close to him above almost everything else.

**Two Months Later**

In May 1960, the creative team was having a difficult time zeroing in on a strategy for one of their clients Belle Jolie Lipstick. As a result, all of the secretaries were asked to gather for a brainstorming session to see if any of the girls could provide some insight into the female thought process. It was following this session that Peggy further distinguished herself from the crowd of secretaries. She made some unique observations to Freddy Rumsen who was particularly impressed with what she had to say. Freddy later suggested to Dick that she be given the opportunity to write copy for that product. Dick didn't see any harm in the idea and he called Peggy into his office to discuss the scheme with her. She was very flattered by the compliment and was excited to be given the opportunity to prove herself.

Peggy worked very hard on her copy for Belle Jolie, often staying past regular working hours to get everything just right. She was careful not to let the extra work interfere with her regular duties. Dick was very impressed with Peggy's work ethic, knowing that she was working harder than most of the male copywriters ever did.

When it came time to present the copy to the client, Dick hit the ball out of the park with the pitch and the client bought the work on the spot. Dick invited Peggy into his office with the rest of the creative team to celebrate their victory with a drink and Peggy happily agreed. Dick couldn't keep himself from staring at Peggy, who was grinning from ear to ear. He thought that she was quite beautiful when she smiled like that. Peggy met his gaze and the two stared at each other for a few moments until she looked anyway.

"Why don't you just ask her out?" Freddy suggested, having observed the entire exchange. "She's a sweetheart, and she's smart as a whip. For what it's worth, I know she admires the hell out of you."

"I'm her boss...it wouldn't be appropriate." Dick said flatly.

Freddy put his hand on Dick's shoulder. "Dick, listen to me. Life is short. If you think you may have found someone that you could be with, that would make you happy, I say forget about your rules and go for it. Things like that don't happen everyday. Well maybe they do to you with your matinee idol good looks, but not for schlubs like the rest of us. You've been alone long enough Dick. You deserve to be happy."

Dick pat Freddy on the back and smiled in appreciation of his encouraging words. Dick said nothing, but he gave what Freddy had said some serious thought.


	6. Chapter 6

**Saving Private Whitman**

(AKA, Dick Whitman pays it forward)

* * *

Blurb: Lieutenant Donald F. Draper resolves to help young Dick Whitman have a better life. AU. Dick Whitman, Lt. Donald F. Draper, Anna Draper, Adam Whitman, Betty Hofstadt, Roger Sterling, Pete Campbell, Freddy Rumsen, Joan Holloway, Peggy Olson. *I OWN NOTHING. MATTHEW WEINER AND LIONSGATE OWN EVERYTHING.

* * *

**Author's Notes: This chapter contains sexual content.**

* * *

**Chapter 6**

Following the Belle Jolie presentation, the other secretaries took Peggy out to celebrate her victory at a bar in midtown after work. An invitation was extended to the entire creative team as well as the account executives. Pete Campbell came along and sat alone in a booth glowering at Peggy as she danced with everyone from Ken Cosgrove to Freddy Rumsen. Dick even went along, which astonished everyone.

Dick sat in a booth with with Freddy and had a few drinks over the course of several hours. Freddy eventually went home and left Dick alone to ruminate. Peggy eyed Dick curiously when she noticed that he was watching her dance with other men. She couldn't for the life of her discern what he was thinking, but to her inebriated mind, it almost appeared as though he was looking at her with admiration. Peggy went over to where Dick was sitting alone nursing his third Old Fashioned.

"Dance with me." she said, fully expecting him to turn her down.

Dick looked at her in silent contemplation. He smiled warmly and said, "I'd love to."

Peggy felt her stomach flutter and she beamed happily as she grabbed his hand and pulled him onto the dance floor. Peggy had to crane her neck in order to see Dick's face as they swayed slowly to the music playing on the jukebox.

"You are incredibly talented Peggy. You know that right? It took me years to be able to think that way, and you nailed it on the first try." Dick said suddenly.

Peggy felt her cheeks grow warm. "Thank you Mr. Whitman."

Dick chuckled. "Peggy, we're not at the office. You can call me by my first name."

"Okay, Dick." Peggy said, blushing even further.

"Peggy, how would you feel about taking on more responsibility? I can't promote you just yet because unfortunately people will talk. But you are too smart and talented to just be my secretary. I think we could relieve you of some of your secretarial duties and allow you to try your hand at a few more accounts. Does that sound like something you'd be interested in doing?"

Peggy beamed "Are you serious?"

Dick nodded. "I am."

"Of course I would be interested! That would be amazing! I mean, I enjoy working for you, but copywriting is such a challenge and I really enjoyed it."

Dick smiled. "I'm glad to hear it."

"Thank you so much for having faith in me!" Peggy said sincerely, her eyes dancing with excitement.

Dick was silent for a few moments as he gazed down at her. He then reached down and gently touched her face. Peggy felt her stomach flutter once again. "You are so different from all of the other girls." Dick said quietly.

Peggy furrowed her brow. "Mr. Whitman...Dick...what are you doing? You're my boss." Peggy stated, feeling a nervous excitement in spite of herself.

Dick touched her lips with his thumb and looked directly into her eyes. "Do you want to know why I said that people will talk?" Dick asked.

"Yes, I did wonder what you meant by that."

"I don't want anyone to think that I gave you something that you haven't earned based on your own merit."

Peggy shook her head in confusion. "I don't understand. Why would they think that?"

Dick's eyes bored into hers and she felt her heart flutter. "Because I'm in love with you Peggy."

Before Peggy knew what was happening, Dick leaned his head down and kissed her softly on the lips. Peggy was in shock, but she quickly recovered and she closed her eyes and returned his kiss. After Dick pulled away a few moments later, she opened her eyes slowly and saw that he was staring at her with wry smile on his face.

"I have wanted to do that for some time now." Dick confessed sheepishly.

Peggy furrowed her brow in confusion. "I don't understand...I thought you never dated anyone from the office."

"Peggy, I don't care anymore. From the first moment we met I felt there was something special about you. I felt a connection with you that I've never felt with anyone before. I have tried to deny my feelings but it's no use. I'm closer to you than anyone in that office and I feel like I can tell you anything. I can't stop thinking about you."

Peggy was astonished. "I had no idea."

Dick continued, "I have been alone for a very long time, but I've been searching for the right woman to spend my life with. I am happy when I'm with you. I can see myself having a family with you, and growing old together." Dick smiled and cupped her cheek. "Now, am I alone here? Do you have feelings for me? Would you like to be with me...not as a boss and his secretary, but as a man and a woman?"

Peggy felt her cheeks grow warm and she hesitated just a moment before answering. "Yes, I would."

Dick grinned and then he grabbed the sides of her face and kissed her full on the lips.

* * *

They left the bar together and Dick accompanied Peggy to her apartment, stating that he didn't want her going all the way to Brooklyn alone. Peggy invited him inside and as soon as they entered the apartment, Dick kissed her passionately on the lips. Peggy ended the kiss after a few moments and pulled him into her bedroom.

"We have to be quiet, I have a roommate." Peggy whispered.

"Are you sure this is okay?" Dick asked quietly.

Peggy nodded, taking off her coat and shoes and throwing them on the chair in her room. She walked over and stood before Dick and she gazed up at him with a look of pure innocence.

Dick took off his jacket and tie and he eyed her curiously. "Peggy, this is your first time isn't it."

Peggy could no longer meet Dick's gaze. "Yes." She said quietly.

Dick sighed. "We don't have to do this tonight. I'm in absolutely no hurry."

Peggy shook her head. "No, I want to." She said emphatically and she looked up and met his eyes. "I love you, Dick. I think I fell in love with you on my first day at Sterling Cooper, when you were so nice to me...and you told off Pete Campbell."

Dick chuckled and he cupped her cheek and looked into her eyes.

"Peggy, you are one of the most genuine people I have ever met. I think you are wonderful. I love you but I need to make sure that you are certain that you want to do this."

Peggy nodded emphatically. "I do, very much."

Dick took her face in both of his hands and kissed her gently at first, and then gradually increased with intensity. He then began undressing Peggy, unzipping her dress, allowing it to pool at her feet. Peggy released her hair from its tie, allowing her hair to fall freely down her back in waves. Dick stepped forward, gently nudging Peggy toward the bed. Dick pulled her slip over her head and Peggy lay down on her back. He kissed her passionately once again and then he unbuttoned and removed his shirt and his pants. Peggy felt her heartbeat increase as Dick kissed her jaw, and then gradually worked his way down to the top of her breasts. Dick unfastened Peggy's brassiere and then slowly removed the rest of her undergarments.

"You are so beautiful." Dick said as he gazed down at her naked body. Peggy felt exposed, but extremely comfortable in front of him. Dick pulled off his undershirt, revealing his broad, bare chest, and be kissed her once more on the lips as he removed his shorts. "I love you, Peggy." Dick said, looking directly into her eyes as he ran his hands over her smooth, shapely legs and up the length of body, cupping her breasts. He then lowered himself on top of her and he slowly and deliberately entered her, allowing Peggy the opportunity to get used to the feeling of having him inside her. Peggy was shocked by the pain and pressure at first, but after a brief period of unpleasantness, she was able to enjoy the feeling of being so physically close to him, having his bare flesh pressed against hers.

"Are you okay?" Dick asked with a look of concern on his face.

Peggy nodded. "Yes...I love you, Dick." Peggy said sincerely.

Dick kissed her again and he gradually began thrusting back and forth, but he was mindful that he needed to be gentle with Peggy since this was her first time. After the initial pain, Peggy began to enjoy herself a little as Dick gradually increased the speed and intensity of his thrusting. Within a few minutes, Dick reached his climax and he collapsed upon top of her.

After a few moments, Dick rolled off of Peggy and lay on his side facing her. Dick leaned over and kissed her tenderly on the lips. "Thank you for that. You are so beautiful, Peggy. I love you, very much."

"I love you too, Dick." Peggy said happily. Dick lay down on his back and he pulled her close. Peggy rest her head on his chest and Dick rest his chin on top of her head. They both fell asleep in each other's arms.

Early the next morning Dick woke up feeling a little disoriented. He smiled when he realized where he was and he looked over at Peggy who was sleeping soundly. Her long brown hair fanned-out in waves across her face and her pillow. She looked like an angel. Dick gently traced the lines of her face with his fingertips and moved her hair off of her face so he could kiss her lightly on her lips. Peggy stirred and opened her eyes. "Good morning, sweetheart." Dick said affectionately.

Peggy smiled. "Good morning, Dick."

Peggy felt a little self conscious when she realized that they were still lying naked in bed together. She pulled her blanket over top of her body in an attempt to preserve her modesty.

Dick noticed this and he touched her face. Peggy, you have nothing to be embarrassed about, you are very beautiful. Were you able to enjoy yourself last night?" Dick asked. "I promise you it will feel better over time."

Peggy blushed prettily. "I did, very much thank you. I am very glad my first time was with you." Peggy said sincerely. She hesitated for a few minutes before asking the next question.

"There has been something that I've been meaning to ask you."

Dick smiled, "Ask me anything."

"What happens now? Do we go back to the way things were with me as your secretary? Should I ask Joan to assign me to someone else?"

Dick furrowed his brow. "Is that what you want Peggy?"

Peggy shook her head emphatically. "No, not at all. But I don't want to make things difficult for you either."

"Let me ask you this. Can you keep a secret?"

Peggy nodded, "Yes, I can. Up until yesterday did you have any idea that I had feelings for you?"

Dick laughed, "No, I did not. You are a great actress. I think we'll be fine, but we have to behave professionally."

"I had another question...were you serious letting me writing copy?" Peggy asked nervously.

Dick nodded. "I was. You are very talented Peggy. You have a perspective that no one else in that office has. You work harder than most of the other copywriters too. Frankly, I think your talents would be wasted if you were stuck sitting at that desk answering my phone all the time. But like I said before, there can't be any appearance of impropriety. Are you still okay with working at my desk most of the time, and then if there are any products that would benefit from a woman's point if view, I will toss them your way?"

Peggy nodded. "Sure. That would be great."

Dick smiled. "Wonderful. I want you to know that I would promote you to right now if I could, but I can't be accused of playing favorites, especially after what just happened between us. Plus I think it's prudent to wait until you get more experience."

"I understand. But what if you do eventually make me a copywriter and people start to wonder how I got the promotion?" Peggy asked.

"Then you'll just have to let your work speak for itself." Dick said wryly.

Peggy smiled. "I think I can manage that."


	7. Chapter 7

**Saving Private Whitman**

(AKA, Dick Whitman pays it forward)

* * *

Blurb: Lieutenant Donald F. Draper resolves to help young Dick Whitman have a better life. AU. Dick Whitman, Lt. Donald F. Draper, Anna Draper, Adam Whitman, Betty Hofstadt, Roger Sterling, Pete Campbell, Freddy Rumsen, Joan Holloway, Peggy Olson. *I OWN NOTHING. MATTHEW WEINER AND LIONSGATE OWN EVERYTHING.

* * *

**Author's Notes: **I apologize for the delay in posting this next chapter. Real life got in the way and I took some time off. Thank you those of you who have read and reviewed this story so far. I really appreciate the feedback. :)

* * *

**Chapter 7**

The morning after:

Dick woke up early the next morning with the intention of slipping out of Peggy's apartment without waking her roommate. Dick quietly got dressed and leaned over and gently kissed Peggy on the forehead, causing her to stir.

"Mmmm..." Peggy groaned, "What's going on? Dick? Are you leaving?"

"Shhh." Dick whispered. "Don't get up. I can show myself out. Go back to sleep sweetheart. I'll see you at the office on Monday. I love you."

Peggy quickly sat up, pulling the sheet up over her body and moving her hair out of her eyes. She smiled, "I love you too, Dick." Peggy said softly.

Dick gently cupped her cheek and kissed her softly on the lips. "Goodbye, Peggy. I had a wonderful time." Dick said softly with a smile.

Peggy yawned and laid back down in her bed. Dick covered her with the blankets and then kissed her lightly once more on the lips. Dick gathered his belongings and quietly left Peggy's bedroom and then her apartment.

For the remainder of the weekend, Peggy's encounter with Dick was never far from her mind. She found that she couldn't regret what they did despite what she had been taught through many years of Catholic school. This wasn't some brief office flirtation, she truly loved him with all of her heart. She hoped that when the time came to see him at work, that she would be able to maintain professional decorum in his presence. She knew that their working relationship would never be the same.

Dick found that he felt a nervous excitement when he arrived at work on Monday and he couldn't keep himself from smiling. Dick politely nodded and greeted everyone in his path on the way to his office. The secretarial pool couldn't help but notice how well Dick's happy mien became him.

Peggy admired his person as he strode through the office and she took note of the extra spring in his step that wasn't usually there. There eyes met when he reached Peggy's desk and Dick smiled warmly.

"Good morning Mr. Whitman." Peggy said brightly.

"Good morning, Peggy." Dick said cheerfully as he handed Peggy his hat and coat. "Did you have a good weekend?"

"Yes I did, thank you Mr. Whitman. How about yourself?" Peggy asked.

"I had a wonderful weekend, Peggy." Dick said sincerely, holding her gaze for longer than was proper in their current setting. Peggy blushed, but then she quickly recovered herself.

"Come into my office so we can discuss this week's schedule." Dick said, gesturing towards his office. Peggy entered and Dick followed closely behind and shut the door.

Once inside his office, Dick led Peggy to the area near his couch which was out of the view of the semi-translucent walls. He then took her in his arms and kissed her passionately.

"I'm sorry, I've been thinking about you all weekend. I missed you." Dick said sheepishly after he ended the kiss several minutes later. Peggy put her hand to her swollen lips but she couldn't help smiling.

"I missed you too, Dick." Peggy said honestly. "But are you sure it's a good idea for me to continue on as your secretary? It seems like you might be tempted to misbehave if I stay put. I could ask Joan to switch me to someone else."

Dick shook his head emphatically. "No, that won't be necessary. That was just a momentary lapse...I can control myself from now on." Dick smiled ruefully. "Anyway, I don't think I could stand it if you were someone else's secretary. I'll behave myself, I promise. How are you doing?"

Peggy chuckled. "Good. I feel like everybody knows about us though...like everybody is staring, watching to see how we're going to interact."

"That's all in your mind Peggy. Nobody knows."

Peggy felt some measure of relief, but she still felt a little uneasy.

"Now...we really should go over this week's schedule Ms Olson." Dick said, changing the subject.

"Yes Mr. Whitman." Peggy said dutifully while locking eyes with Dick who gave her a knowing smile.

After his initial lapse in propriety, Dick was able to keep his relationship with Peggy strictly professional while in the office. They would occasionally exchange meaningful glances while in the presence of the other executives, but it was never enough to draw anyone's notice. Behind the closed door of his office there was the occasional chaste kiss, and once in a while Dick's hand would "accidentally" brush up against Peggy's and then he would squeeze her hand as a result. But there was never any huge breech of propriety that could accidentally expose their relationship. The other executives did take notice of Dick's improved mood, but they never suspected that Peggy was the reason for it.

That weekend Dick took Peggy out for an actual date. They decided to stay in Brooklyn for the evening to ensure secrecy. They had an early dinner out and then went to the movies. Dick picked Peggy up at her apartment and was formally introduced to the roommate. They made love that night and once again Dick stayed overnight at Peggy's apartment. This time however, Peggy insisted that he stay and have breakfast with her before she went to Mass.

Things continued in a similar manner for several weeks. Dick invited Peggy to his apartment one evening and introduced her to his brother Adam. Adam took to her immediately and the two of them got along very well.

"You must be very special to him Peggy. I don't think Dick's ever brought another girl home to meet me." Adam said matter-of-factly.

Peggy had a difficult time detecting any familial resemblance between the two half brothers. While Dick had dark brown hair and a tan complexion, Adam had red hair and freckles. They both were however about the same height as they had the same green eyes.

Adam explained that he was working most nights as a janitor in the Empire State Building and he was going to school during the day.

"What are you studying?" Peggy asked.

"I'm learning to be an auto mechanic. I've always been good with my hands...Dick got all of the book smarts. But it's good money and hopefully once i'm done with school I can quit being a janitor and find a great job so I can try to pay Dick back for all he's done for me. I'm just so grateful that he's taken me in. I don't want to think about where I would be if he hadn't let me move in with him." Adam said with great feeling.

"He's a good man isn't he?" Peggy said as she looked lovingly at Dick as he prepared their dinner in the kitchen. As if sensing that he was the topic of conversation, Dick looked in their direction and smiled. He was happy to see that two of the most important people in his life were getting along so well.

"He's the best." Adam said emphatically.

Later that night in the privacy of his bedroom, Dick opened up more about his past, revealing that he and Adam had in fact been raised in a brothel. Peggy was horrified, but she realized how ashamed Dick must feel about his past. She admired him for having the resolve to overcome such seemingly insurmountable obstacles to make a better life for himself and Adam. She was honored that Dick trusted her enough to be completely honest with her about his past and she promised to keep his secret forever.

Due to Adam's busy schedule, he was hardly ever home when Dick was, thus Dick often had the apartment to himself all night. It eventually became quite commonplace for Dick and Peggy to stay at his apartment most nights of the week. They would stay at her own place on Saturday nights so that she could be seen at her church on Sunday and remain in her mother's good graces.

**Eight Weeks Later**

Things continued to go very well in Dick and Peggy's relationship. They spent practically every night together but they managed to keep their relationship a secret at the office.

One morning Peggy became ill and she stayed home from work. She continued to feel poorly for the next several days and she missed work for a week. Dick was concerned and insisted that she see a doctor to find out what was wrong. The doctor ran some tests and when he called with the results she was surprised to find out that she was pregnant.

Dick was overjoyed when she told him the news. "Peggy I know you are probably upset, but I couldn't be happier. I was planning on asking you this very soon anyway, but will you marry me?"

Peggy was relieved. "You want to marry me?"

Dick grinned. "I do, very much. I love you Peggy. This just feels right. All I've wanted for the longest time was to have a wife and a family...just to have the sort of stability in my life that I never had growing up. I'm now in the position financially to provide very well for a wife and however many kids that should happen to come along, I just hadn't met the right person yet. But you're the one Peggy. I'm thrilled with this news! I knew there was something special about you from the first moment we met. I want to marry you spend the rest of my life with you."

"My mother is going to kill me...and you too actually!" Peggy said dramatically. Dick grimaced.

"Did the doctor say how far along you are?" He asked.

"About nine weeks or so. Ugh, there's no way that this can explained without me looking like a strumpet."

Dick frowned. "I don't ever want to hear you use that word to describe yourself again. You did nothing wrong. You love me right?" Peggy nodded. "And this baby is a result of that. I don't care what those nuns and priests taught you. You are a good person Peggy and you are going to be a wonderful mother."

Peggy began to cry and Dick folded her into his arms. "Shhh, Peggy. Please don't cry. Everything will be fine. We can get married as soon as possible at City Hall, and tell people we eloped if you like. No one would be the wiser except for Adam and your roommate...and Freddy."

"Freddy? How does he know about us?" Peggy asked with alarm.

"Freddy is the one who encouraged me to forget my rules and ask you out. He saw me admiring your beautiful smile and told me I should just go for it. That was the best advice I have ever been given." Dick said with a warm smile. "But you never answered my question Peggy. Will you marry me?"

Peggy wiped away her tears and looked into Dick's eyes. "Are you sure this is what you want?" Peggy asked.

Dick nodded. "Absolutely. I love you Peggy. I knew I wanted to marry you after our first night together. We'll make it work...I want to raise a family with you."

Peggy gazed at the amazing man in front of her with happy tears glistening in her eyes. "Then yes Dick Whitman, I would be happy to marry you."


	8. Chapter 8

**Saving Private Whitman**

(AKA, Dick Whitman pays it forward)

* * *

Blurb: Lieutenant Donald F. Draper resolves to help young Dick Whitman have a better life. AU. Dick Whitman, Lt. Donald F. Draper, Anna Draper, Adam Whitman, Betty Hofstadt, Roger Sterling, Pete Campbell, Freddy Rumsen, Joan Holloway, Peggy Olson. *I OWN NOTHING. MATTHEW WEINER AND LIONSGATE OWN EVERYTHING.

* * *

**Chapter 8**

The evening after he became engaged, Dick made the long distance telephone call that he had been waiting to do for some time.

"What are you and Don doing a week from Monday?"

"I don't know Dick. Why? What do you have planned?"

Dick smiled broadly. "I'm getting married and I would love for you and Don to be there. Aside from Adam, you are the only family I have and I want you to be here."

Anna smiled. "Oh Dick, that's wonderful! Who is she?"

"Her name is Peggy, and I met her at work...she's my secretary."

"You fell in love with your secretary? How romantic."

Dick chuckled. "I know it's a cliché, but she's different. You'd like her. She's pretty and smart and funny...she reminds me of you actually."

"Ah, so this one will keep you on your toes. I'm so happy for you Dick!"

Dick cleared his throat. "There's more...I'm going to be a father." Dick said happily.

"So soon?" Anna said with a note of disapproval. "No, I'm sorry Dick. I shouldn't have said that. I'm not your mother. That is wonderful news!"

"Thank you. I couldn't be happier. What do you say, will you and Don be there. It would mean so much to me if you were."

"Of course we'll be there. I wouldn't miss it for the world. Congratulations Dick. I'm so happy for you!"

* * *

Peggy knew that it wasn't going to get any easier the longer she waited to tell her mother about her pending nuptials. She brought Dick with her when she went over to her sister's house to speak with her mother.

"Ma, I'd like to introduce you to my fiancé, Dick Whitman. Dick, this is my mother Katherine Olson."

Mrs. Olson looked quizzically at her youngest daughter and the tall handsome man before her. "Fiancé? Since when? You've never even mentioned that you were seeing someone. How can you be engaged?"

Dick frowned and Peggy grabbed his hand and gave it a reassuring squeeze. "Ma," Peggy said with exasperation, "we've been dating for a while..."

"Then how come I've never met him?" Katherine interrupted. "How old are you Dick, if you don't mind me asking?"

"Thirty-five, Mrs. Olson." Dick answered politely.

"Really? And you've never been married?"

"No Ma'am."

"Hmmm." Katherine said, furrowing her brow. "And how did you two meet?"

"We met at work Ma." Peggy explained.

"Let me guess Mr. Whitman...you took advantage of your secretary and now she's pregnant."

"Ma!" Peggy exclaimed.

"I'm sorry Peaches, but I wasn't born yesterday. I know what goes on in the city."

Peggy was mortified and looked at Dick apologetically. Dick squeezed her hand and smiled reassuringly.

"Mrs. Olson, you have every right to be skeptical of men like me. Yes, Peggy is my secretary and she is carrying my child..."

Mrs. Olson harrumphed and twisted her face into a scowl.

"...but I want you to know that I would marry your daughter regardless of her condition. I love her."

Mrs. Olson glared at her daughter and her suitor. "Margaret, what would your father say?"

"I know Dad wouldn't be pleased, but don't you think he would want me to be happy? Dick makes me very happy. He's a good man...Dad would've like him."

Mrs. Olson sighed deeply. "Well you can't get married in the church...not under these circumstances."

"I know Ma. We're planning on city hall a week from Monday. Please say you'll be there."

Mrs. Olson shook her head and sighed, "I don't know, Peaches."

"Mrs. Olson if I may," Dick interjected, "I know these circumstances aren't ideal. But you need to know that I will take care of your daughter. I make a good living at Sterling Cooper and your daughter and our children will want for nothing. I was alone for a very long time, but I think I was just waiting for your daughter to come along and sweep me off my feet. I love your daughter and it would mean a lot to her...to us if you would give us your blessing and come to our wedding."

Mrs. Olson looked between her daughter and her soon to be son-in-law and smirked. "You're right Peaches. Your father would've liked him."

Dick smiled and felt a sense of relief. Katherine reached out and shook his hand firmly.

"I'll come to the wedding...on one condition." Mrs. Olson said finally.

Peggy furrowed her brow in confusion. "What condition Ma?"

"I want to go with you to pick out your dress. This may be a quickie wedding, but you are still my little girl and you'll only get married once."

Peggy's eyes filled with happy tears. "Of course Ma. That would be lovely." Peggy threw her arms around her mother's shoulders. "Thank you." Peggy said gratefully.

"There's one more thing." Mrs. Olson said suddenly. "I'm assuming you live in the city Dick, but I insist that you move to Brooklyn so that I can help out my daughter when the baby comes. There are lots of pretty houses here in Bay Ridge that you can fill with kids."

Dick smiled uncomfortably and looked to Peggy for help. Peggy smirked, "You said you longed for a big family, Dick. You won't find more family togetherness than with the Olson clan."

* * *

Dick and Peggy obtained a blood test and a marriage license and were married on Monday August 15th at City Hall surrounded by a small group of friends and family. Don and Anna Draper were able to fly in and witness the wedding of their close friend, and Dick was pleased to be able to introduce the two most influential people in his life to his brother and his new wife.

"Thank you so much for coming sir." Dick said as he hugged his former commanding officer and friend.

"I wouldn't have missed this for the world Dick. Congratulations!" Don said sincerely.

Dick beamed with pride as he made the introductions. "Donald and Anna Draper, I would like to introduce you to my brother Adam, and my beautiful wife Peggy Whitman." Dick said proudly.

Don kissed the bride on the cheek and then moved on to chat with Adam. Anna drew Peggy into a warm embrace.

"Congratulations Mrs. Whitman! Dick has told me a lot about you."

"Thank you! And the pleasure is all mine Mrs. Draper. Dick talks about you and your husband often. I think I'll forever be indebted to you for taking an interest in him. Who knows, if it hadn't been for you, we may never have met."

Anna waved Peggy's gratitude off. "Oh please, none of that. We were glad to do it. Don and I love Dick like family. I hope that we can become close as well."

Peggy grinned. "I would like that. And please call me Peggy...it's going to take some time getting used to being called Mrs. Whitman!"

"Peggy it is. And you must call me Anna."

* * *

Dick and Peggy spent their wedding night at _The Pierre_ and they both took the remainder of the week off of work in order to move Peggy's things into Dick's apartment and enjoy their first days as husband and wife.

They both returned to work the following Monday, arriving together for the first time without any reservation. Peggy felt as though the eyes of the entire office were on her as she entered side-by-side with Dick. Almost immediately after she arrived at her desk, Joan approached her in a snit.

"It was very presumptuous of you Peggy to take off work at the same time as your boss. You were needed here in the office."

Peggy looked to Dick with alarm and he quickly came to her rescue.

"Joan, I apologize for taking Peggy away from her duties last week. I wish we could have taken more time off for a honeymoon, but that wasn't possible."

"I beg your pardon?" Joan said with confusion.

"I'm sorry, I guess I wasn't clear. Peggy is my wife. We got married last week." Dick said proudly as he put his arm around Peggy and kissed her temple.

Joan was speechless. Dick took that as an opportunity to grab Peggy's hand and lead her into his office while Joan continued to stand at Peggy's desk completely dumbfounded.

* * *

It was unsurprising that there was an uproar at work when it was revealed to the general population that Don and Peggy had gotten married. Peggy received many dirty looks from the other secretaries and several even refused to speak to her. Joan was shocked and a little jealous. Later that afternoon Joan approached Peggy on the break room to try to ferret out more information.

"I don't know how you did it. I mean no offense, but he never even looked at me. I thought for sure he was a homosexual."

Peggy bristled and she couldn't resist a dig at Joan's expense.

"I can assure you he isn't. I guess you just aren't his type." Peggy said smugly.

Joan smirked, "Well now that you're married to him, you are going to need to stop dressing like a little girl and begin to act the part of the perfect housewife. I'm sure he's not going to want his wife to be his secretary anymore. I'm quite envious because now you can afford a whole new wardrobe you lucky girl!"

Peggy smiled tightly. "I realize you think you're being helpful, but I know Dick and he doesn't care about superficial things like that. And he'll be happy for me to work for him up until it's no longer comfortable for me to do so."

Joan was left speechless once again, wondering what exactly Peggy was implying with her cryptic remark.

The only person in the office who was genuinely happy for Dick and Peggy was Freddy. He took them aside in Dick's office and congratulated them.

"I couldn't be happier for you both. I've known this guy for a lot of years Peggy, and you've got yourself a good man. I don't think I've ever seen him as happy as he's been since he's been with you...which brings me to another point. I know this is none of my business, but if I recall, Dick you were mooning over Peggy after the Belle Jolie pitch. Now, two months later you're married? Am I right in assuming that there will be another congratulations in order...say in about seven months?"

Peggy turned beet red and looked at her feet.

"You would be right in assuming that Freddy." Dick said with a rueful smile.

Freddy pat Dick on the back. "Well, that is truly wonderful news. I want to wish you both the best of luck. For what it's worth, I think you're going to wonderful parents."

Going public at work had its advantages in that now Dick and Peggy could be affectionate in the office within reason. Dick would occasionally kiss her lightly on the cheek and affectionately squeeze her hand in full view of the office. He was also very solicitous of her comfort, especially when it appeared that she was feeling unwell due to her condition. Most of the secretaries resented Peggy's good fortune, especially once they saw what a loving husband Dick was turning out to be. As time went on, many of the male executives took notice of the subtle changes in her figure with great interest and appreciation.

Peggy continued to work as Dick's secretary and she was excited to be asked to write copy for a product that was geared towards women, which was a weight loss belt. She was mortified when she had to explain to her husband what the product actually did.

"Peggy, I can't help you if you don't put into words exactly what the thing does."

"Well Dick, let's just say that it stimulates a woman in a way that renders a man unnecessary."

Dick's eyebrows shot up, "Really?"

Peggy nodded, "Yes, really."

Dick helped her to elegantly put into words what the unintended benefits of the product were. As with Belle Jolie, Peggy's copy went over very well with the client and Dick was exceedingly pleased that he had his wife's considerable talent at his disposal.

* * *

Unfortunately Roger Sterling suffered a major heart attack over the Labor Day weekend and it was unknown whether or not he would survive. Bert Cooper decided to put the clients at ease by naming Dick as a new junior partner. This required significantly more responsibility on his part, but with the promotion came a substantial raise. Dick finally felt comfortable purchasing a house and he found one in Brooklyn near Peggy's family in Bay Ridge. There was enough room in the house for Adam as well and Dick happily invited his brother to stay with him and his wife for as long as he needed.

By November Peggy was noticeably showing and everyone in the office knew that she was pregnant. Dick often found himself staring at his very pregnant wife with admiration. He thought that she had never looked more beautiful.

The other secretaries eventually got over their resentment of Peggy and threw the Whitman's a joint baby shower in conjunction with the Christmas party.

The couple rang in the new year together and a several weeks later Peggy's due date was upon them. Peggy went into labor and on February 4th 1961, Dick and Peggy welcomed their daughter Anna Elizabeth Whitman into the world.

Don and Anna came to visit shortly after the baby was born and Dick and Peggy asked them to serve as their daughter's godparents which they happily agreed to.

At the urging of her husband and mother, Peggy quit her job at Sterling Cooper in order to be home with the baby. She missed going to work everyday with her husband, but Dick came home every night and was excited to spend time with his wife and daughter. With his marriage and the arrival of his baby girl, Dick finally felt as though his life was complete.


	9. Epilogue

**Saving Private Whitman**

(AKA, Dick Whitman pays it forward)

* * *

Blurb: Lieutenant Donald F. Draper resolves to help young Dick Whitman have a better life. AU. Dick Whitman, Lt. Donald F. Draper, Anna Draper, Adam Whitman, Betty Hofstadt, Roger Sterling, Pete Campbell, Freddy Rumsen, Joan Holloway, Peggy Olson. *I OWN NOTHING. MATTHEW WEINER AND LIONSGATE OWN EVERYTHING.

* * *

**Epilogue**

Over the span of eleven years, the Whitmans had six children, making Katherine Olson the happiest grandmother there ever was. She loved her grandchildren and was a tremendous help to her daughter through her many pregnancies. Katherine grew very fond of her handsome son-in-law and was happy to see that he treated her daughter and grandchildren very well.

Dick turned out to be a very doting husband and father. He made a concerted effort to be home at a reasonable hour every night so that he could tuck his children in and read them a bedtime story. Over time, Dick became a full partner at Sterling Cooper. Eventually the agency was bought by McCann-Erickson, whose sole interest in the firm was Dick and his creative work. While Dick wasn't thrilled about working for a sausage factory like McCann, the sale of the agency made him a very rich man.

Dick was sort of an anomaly in the ad world in that he was a happily married family man. He avoided the trappings that many ad men fell victim to. While he was a smoker, he wasn't a heavy drinker, wanting to avoid becoming like his father at all costs. He also managed to remain faithful to his wife unlike many of his colleagues. The Whitmans remained happily ensconced in their Brooklyn brownstone for many years, seeing no reason to move. The children all attended the same parochial school that their mother attended when she was a girl and the commute was a fairly easy one for Dick.

Peggy found that she relished being a wife and mother and she didn't really miss going to work with her husband...much. Dick would often ask for her opinion on his creative work and she was happy to oblige. He even credited her with the kernel of an idea that won him his first Clio award. Dick knew that if things had been different, that Peggy would have been a force to be reckoned with in the advertising field. But as it were, he was happy that he could count on her as his agency's "secret weapon".

Over the years Peggy became accustomed to being a housewife and she couldn't believe how blessed she was to have found such a loving husband. They made love often, which resulted in their six children Anna, Mary, Donnie, Matthew, Danny and Jimmy. Luckily for the family, when Sterling Cooper was sold to McCann, Dick's partnership was worth three quarters of a million dollars. Dick saved quite a bit of the money for the children's college funds and Peggy never again had to worry about their futures. The family lived modestly in Brooklyn, and though they had their fair share of ups and downs, Dick and Peggy had a very happy marriage.

Dick's brother Adam got a job working as a mechanic at a local garage and he eventually moved into his own apartment. He married a local girl named Debbie and started a family of his own. Adam's job at the garage paid well and he was able to support himself and his wife and three kids. Adam also remained in Brooklyn, and Dick was pleased to see that his brother was able to do so well for himself.

Peggy became close friends with Anna Draper and the two women regularly wrote to one another. Don and Anna were present for the Christenings of most of the Whitman's children and they served as the godparents for three of the kids.

As the years went on and familial obligations began to take up much of their free time, the Whitmans began to lose touch with the Drapers a bit. By the time of the baptism of their sixth child Jimmy, Dick and Peggy hadn't heard from Don and Anna in close to a year. Dick decided to call them one evening, and he was dismayed to hear from Don that Anna was very sick and that she wasn't expected to live for much longer. Even though several of their children were still quite young, Dick and Peggy flew out to California with their entire family to visit Anna in the hospital and to say goodbye.

Dick entered the hospital room and saw Anna lying in her bed looking very small and frail. His heart clenched with sadness when he noticed Don sitting by her bedside asleep and holding her hand.

"Knock, knock." Dick said quietly so as not to startle them.

"Hey there stranger!" Anna said enthusiastically, smiling warmly. Don remained asleep in the chair. It was evident that he had been holding vigil at Anna's bedside for some time.

"Peggy and the kids are back at the hotel. They all want to visit you but I wanted to make sure that it wouldn't be too much for you."

"Oh Dick, I would love to see them. I'm so glad that you came all the way out here! How are you? You look good."

Dick chuckled. "Only you would ask about my well being at a time like this."

Anna smiled sadly. "Dick, I know I'm dying. I have no regrets and I've lived a good life. I see no reason to dwell on morbid thoughts any longer than necessary. Now, you've traveled a long way to visit me and I want to know all about you and your family."

Dick smiled and told Anna a multitude of stories involving the numerous scrapes his children had gotten in over the years. He was also proud to tell her about how his agency was flourishing since he had become a senior partner.

Don eventually awoke and after briefly greeting Dick, excused himself to eat in the hospital cafeteria. Dick to the opportunity to move into the chair that Don vacated and gently took Anna's hand. Anna smiled warmly at Dick as he kissed her hand.

"Well Dick, you really have made quite a life for yourself. I'm so proud of you."

Dick could feel himself becoming overwhelmed with emotion. He wanted to remain composed in front of Anna, but he was failing miserably. He blinked back the tears that were threatening to fall and cleared his throat before beginning to speak again.

"Listen Anna. I know you don't want to hear this, but there are a few things I need to say. I owe everything I have, everything I've ever achieved to the generosity of you and your husband. You and Don did more for me than my own father ever did. You both showed me what it meant to have unconditional love and support and because of that, I am a better husband and father than I could have ever have hoped to be. I have loved you both like family for twenty years and I don't know what I'm going to do if you're not in my life anymore." Dick could no longer fight the tears that came streaming down his face and he had no wish to. He needed Anna to understand his much she meant to him.

Anna's eyes filled with tears and she placed her hand on Dick's cheek. "Oh Dick, I love you too. I don't have the strength to argue with you over who deserves the credit for your success, but please don't sell yourself short. **You** are the one who worked so hard taking those night school classes, improving your education. You always had the brains and the talent to be successful, we just gave you a little boost. But I do appreciate your kind words. I'm so glad that Don insisted that we take you in. Knowing you and your beautiful family has enriched our lives so much."

Both Dick and Anna were openly crying now. Dick found a box of tissues in Anna's room and he handed her a couple so that she could wipe away her tears and blow her nose. Dick did the same and neither of them spoke for a while.

"Listen Dick," Anna said finally, "I need you to do a favor for me."

"Anything, just name it." Dick said, attempting to regain his composure.

"Please look out for Don. He's trying to put up a brave front but I don't know how he is going to handle it when I'm gone."

"I will. It is the least I can do."

Dick and Anna continued to talk until visiting hours were over for the day. The next day Dick brought Peggy and their children to visit with Anna one last time. She enjoyed seeing the children and before they left the hospital, Anna asked to speak with Peggy alone.

"Peggy, take care of him. I know I don't need to tell you what a good man he is. You and the kids have done wonders for him and he loves you more than life itself. I'm so glad he found you."

Anna Draper died on May 25, 1972. Dick was devastated and it took quite a while for him to recover from the loss. Peggy was a great deal of support to Dick during this time and she enabled him to grieve and cope with the tremendous loss of his close friend. True to his word Dick kept in regular contact with Don and he and the family went out to California every summer to visit him.

Dick never forgot the kindness and generosity of Donald and Anna Draper. He remained grateful to them for the remainder of his life and he strove to instill the values that he learned from them in his own children.

~THE END~


End file.
